Triethylamine → 3-(5-Fluoropyridin-3-ylethynyl)-benzonitrile

HRID 606850Notes

Reaction equation

HRID 606850 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:12]=[N:13][CH:14]=1.[C:23]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29])#[CH:24]>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]([C:24]#[C:23][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])[CH:12]=[N:13][CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl esterHCID 120889643-Ethynylbenzonitrile

Product 1

HCID 670478573-(5-Fluoropyridin-3-ylethynyl)-benzonitrileYield 35%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Add triethylamine (0.79 mL, 5.64 mmol), copper (I) iodide (15.43 mg, 0.08 mmol) and bis(triphenylphosphine)palladium (II) dichloride (49.48 mg, 0.07 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoropyridin-3-ylester, (prepared as described in PREPARATION 6), (345 mg, 1.41 mmol) and 3-ethynylbenzonitrile, prepared as described in PREPARATION 8), (230 mg, 1.41 mmol) in ethyl acetate (2 mL). Stir in a sealed tube at 70° C. for 18 h. Concentrate and purify by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate, to give the title compound (109 mg, 35%).

Workup

  1. customprepared
  2. concentrationConcentrate
  3. custompurify by silica gel chromatography
  4. washeluting with 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-00e5dd7316bb4fc49f1332edc1ae2be3
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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